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Supramolecular Self-associating Amphiphiles: Determination of molecular self-association properties and calculation of critical micelle concentration using a high-throughput, optical density based methodology

Rutkauskaite, Andzelika, White, Lisa J., Hilton, Kira L.F., Picci, Giacomo, Croucher, Lorraine, Caltagirone, Claudia, Hiscock, Jennifer R. (2022) Supramolecular Self-associating Amphiphiles: Determination of molecular self-association properties and calculation of critical micelle concentration using a high-throughput, optical density based methodology. Organic & Biomolecular Chemistry, (20). pp. 5999-6006. ISSN 1477-0520. (doi:10.1039/D2OB00066K) (KAR id:93052)

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Official URL:
http://dx.doi.org/10.1039/D2OB00066K

Abstract

Supramolecular self-associating amphiphiles are a class of amphiphilic salt, the anionic component of which is ‘frustrated’ in nature, meaning multiple hydrogen bonding modes can be accessed simultaneously. Here we derive critical micelle concentration values for four supramolecular self-associating amphiphiles using the standard pendant drop approach and present a new high-throughput, optical density measurement based methodology, to enable the estimation of critical micelle concentrations over multiple temperatures. In addition, we characterise the low-level hydrogen bonded self-association events in the solid state, through single crystal X-ray diffraction, and in polar organic DMSO-d6 solutions using a combination of 1H NMR techniques. Moving into aqueous ethanol solutions (EtOH/H2O or EtOH/D2O (1[thin space (1/6-em)]:[thin space (1/6-em)]19 v/v)), we also show these amphiphilic compounds to form higher-order self-associated species through a combination of 1H NMR, dynamic light scattering and zeta potential studies.

Item Type: Article
DOI/Identification number: 10.1039/D2OB00066K
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Depositing User: Jennifer Hiscock
Date Deposited: 04 Feb 2022 15:09 UTC
Last Modified: 03 Aug 2022 11:32 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/93052 (The current URI for this page, for reference purposes)
Caltagirone, Claudia: https://orcid.org/0000-0002-4302-0234
Hiscock, Jennifer R.: https://orcid.org/0000-0002-1406-8802
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